3483-15-6

Basic information

• Product Name: 3-(o-Methoxyphenyl)sydnone
• Synonyms: 3-(2-Methoxyphenyl)sydnone;3-(o-Methoxyphenyl)sydnone
• CAS NO: 3483-15-6
• Molecular Formula: C₉H₈N₂O₃
• Molecular Weight: 0
• Mol File: 3483-15-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(o-Methoxyphenyl)sydnone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(o-Methoxyphenyl)sydnone(3483-15-6)
• EPA Substance Registry System: 3-(o-Methoxyphenyl)sydnone(3483-15-6)

Safety Data

• Hazardous Substances Data: 3483-15-6(Hazardous Substances Data)

Usage

General Description

3-(o-Methoxyphenyl)sydnone is a chemical compound that belongs to the sydnone family. It is a yellow, crystalline substance that is used in the field of organic chemistry as a precursor for various pharmaceuticals and dyes. The o-methoxyphenyl group attached to the sydnone ring makes this compound useful in synthesizing various derivatives with potential biological and pharmacological activities. It is also being studied for its potential application in the treatment of cancer and other diseases. Additionally, 3-(o-Methoxyphenyl)sydnone has shown antimicrobial and antioxidant properties, making it a compound of interest for further research and development in various scientific and industrial fields.

Upstream product

• 578-57-4 2-bromoanisole 
• 69825-50-9 ethyl 2-((2-methoxyphenyl)amino)acetate 
• 90-04-0 2-methoxy-phenylamine 
• 121163-59-5 N-(2-methoxy-phenyl)-N-nitroso-glycine 
• 108-24-7 acetic anhydride 
• 94800-23-4 (2-methoxyphenyl)glycine 

Downstream Products

• 269392-84-9 3-(2-methoxy-phenyl)-5-methyl-3H-[1,3,4]oxadiazol-2-one 
• 156333-02-7 C₁₁H₁₀N₂O₄ 
• 60642-51-5 3,3'-bis-(2-methoxy-phenyl)-4,4'-sulfanediyl-bis-sydnone 
• 14606-02-1 4-bromo-3-(2-methoxy-phenyl)-sydnone 

Relevant articles and documents

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

Synthesis and evaluation of phenyl substituted sydnones as potential DPPH-radical scavengers

A series of phenyl substituted sydnones has been synthesized and their radical-scavenging activity has been studied on DPPH free radical. Out of eighteen compounds screened, nine compounds show interesting activity. A mechanism is presented whereby sydnones scavenge DPPH radical through donating H-atom at 4th-position. Its strong radical-scavenging activity mainly arises from 1, 2, 3-oxadiazolium-5-olate ring. Different substituents and their positions on the phenyl ring differently influence DPPH scavenging activity and therefore, may provide clues to design and develop better free-radical scavenging sydnones with multiple activities.

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS) as an efficient promoter for one-pot conversion of N-arylglycines to sydnones in the presence of NaNO2/Ac2O under neutral conditions

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS)-promoted one-pot conversion of various N-arylglycines to sydnones using a combination of NaNO2 and Ac2O has been achieved efficiently through N-nitrosation followed by cyclization